CN110945669A - Color-tunable organic light emitting diode device based on single emitter and method thereof - Google Patents

Color-tunable organic light emitting diode device based on single emitter and method thereof Download PDF

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CN110945669A
CN110945669A CN201880048165.2A CN201880048165A CN110945669A CN 110945669 A CN110945669 A CN 110945669A CN 201880048165 A CN201880048165 A CN 201880048165A CN 110945669 A CN110945669 A CN 110945669A
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支志明
毛茂
程刚
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University of Hong Kong HKU
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum

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Abstract

Methods of using and fabricating voltage-dependent color-tunable OLED devices using single platinum emitters are described herein. The platinum emitter may be a pt (ii) complex. The single platinum emitter is mixed with the host material in the emissive layer of the OLED device. The emissive layer may comprise a single high concentration emitter or may comprise two sublayers, one with a low emitter concentration to produce monomer emission and the other with a high emitter concentration to produce excimer emission. When a voltage is applied to the OLED, the device emits a different color. Also disclosed herein are devices comprising platinum emitters and methods of making and using platinum emitters.

Description

Color-tunable organic light emitting diode device based on single emitter and method thereof
Cross Reference to Related Applications
This application claims the benefit of U.S. provisional application No. 62/534,417 filed on 2018, 7/19, which is hereby incorporated by reference in its entirety.
Technical Field
The disclosed invention is generally in the field of Organic Light Emitting Diodes (OLEDs). More specifically, methods of using and making voltage-dependent color-tunable OLED devices using single platinum emitters are described herein. Also disclosed herein are devices comprising such platinum emitters.
Background
The use of white light emitting materials in lighting and displays has attracted considerable attention. In particular, white light may be generated by organic light emitting diodes ("OLEDs"), which are solid state thin film devices consisting of stacked organic layers sandwiched between two electrodes. Light is generated in an electroluminescent layer comprising an emitter, such as a metal complex or a polymer. White light emission can be obtained by: by mixing the three primary colors (i.e., red, green, and blue) or two complementary colors from different emitters disposed within an emissive layer, or by constructing a device structure with multiple emissive layers, or by constructing two or more sub-OLEDs that are combined together.
However, the use of two or more emitters or three or more emissive layers or two or more sub-OLEDs has a number of disadvantages. First, each additional OLED assembly or subassembly adds to the complexity and cost of the OLED. Furthermore, at typical luminance of OLED illumination (i.e., 1000-2) Such an arrangement, in turn, suffers from strong roll-off (run-off), low external quantum efficiency ("EQE"), high drive voltage, and low color rendering index ("CRI") of between 40-70 CRI (due to narrow emission band). The currently used methods for color tunable white OLEDs cannot reach over 20,000cd/m2The maximum brightness of (c).
The present disclosure is provided to address these and other problems.
Disclosure of Invention
Compounds, devices, and methods useful for voltage tuning OLED devices are disclosed. A method for voltage tuning an OLED device is disclosed, the method comprising: providing a first voltage to the OLED device to cause the OLED device to emit a first color having a first wavelength; the first voltage applied to the device is adjusted to a second voltage to cause the OLED device to emit a second color having a second wavelength. In some forms the OLED device has a pair of electrodes having opposite polarities and a plurality of organic layers disposed between the pair of electrodes. In some forms at least one of the plurality of organic layers is an emissive layer, and the emissive layer includes a single emitter mixed with one or more host materials. In some forms, the emitter is a fluorescent or phosphorescent organic light emitting material or metal complex, and the emitter has both a monomer state emission and an aggregate state emission. In some forms the difference between the first voltage and the second voltage is 1V. In some forms the first voltage is 2.4V or higher.
Also disclosed is a method for manufacturing a voltage tunable OLED device, the method comprising: obtaining an emitter, wherein the emitter is a fluorescent or phosphorescent organic light emitting material or metal complex, and the emitter has both a monomer state emission and an aggregate state emission; the emitters are mixed with one or more host materials to build up an emissive layer. In some forms the emitter layer has a weight percentage of emitters of 2-30%. In some forms the OLED device has a pair of electrodes having opposite polarities and a plurality of organic layers disposed between the pair of electrodes. In some forms at least one of the plurality of organic layers is an emissive layer.
In some forms, the emitter has the following chemical structure:
Figure BDA0002373678050000031
in some forms the emitter layer has a weight percentage of emitters of 2-6%. In some forms the emitter layer has a weight percentage of emitters of 16-30%. In some forms the method further includes mixing the emitter with one or more host materials such that the emissive layer includes a first sub-layer and a second sub-layer. In some forms the weight percentage of emitters of the first sublayer is 2-6%. In some forms the weight percentage of emitters of the second sublayer is 16-30%.
In some forms the first sub-layer comprises one host material and the second sub-layer comprises two host materials. In some forms the first sub-layer comprises two host materials and the second sub-layer comprises two host materials. In some forms the first sub-layer emits singlet state emission and the second sub-layer emits aggregate state emission.
In some forms, the one or more host materials are selected from the group consisting of: TcTa, MCP, B3 PymPmm and 26 Dczppy. In some forms, the OLED device is voltage-driven, color-tunable between 2.4V to 14V. In some forms the method further includes constructing the plurality of organic layers to include a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
In some forms, the emitter has a chemical structure according to:
Figure BDA0002373678050000041
wherein X is independently a 5 or 6 membered heterocyclic ring,
wherein R is1-R3Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto (thio), styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl groups,
wherein R is4Independently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonylRadicals, carboxylic acids, esters, nitriles, sulfonyl radicals, phosphino radicals, and combinations thereof,
wherein R is1-R3Wherein each pair of adjacent R groups is independently one or two separate groups or atoms or fused to form a 5-6 membered ring, and
wherein R is1-R4 represents mono-, di-, tri-, tetra-or unsubstituted.
In some forms, the emitter has a chemical structure according to:
Figure BDA0002373678050000051
wherein X is selected from
Figure BDA0002373678050000052
Figure BDA0002373678050000053
And substituted groups thereof;
wherein R is5-R9Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, alkoxycarbonyl, ethyl, butyl, tert-butyl, -C- (CH)3)3、
Figure BDA0002373678050000054
(3, 5-di-tert-butyl) Ph, fluorine,
Figure BDA0002373678050000055
Wherein R isxAnd RyIndependently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, aminomethylAcyl, aryloxycarbonyl, phenoxycarbonyl, alkoxycarbonyl, ethyl, butyl, tert-butyl, -C- (CH)3)3, (3, 5-di-tert-butyl) Ph, fluorine or
Figure BDA0002373678050000056
And
wherein R is5-R8Each pair of adjacent R groups in (a) is independently one or two separate groups or atoms or fused to form a 5-6 membered ring, and
wherein R is5-R9Represents single, double, triple, quadruple or no substitution.
In some forms, the emitter has a chemical structure according to:
Figure BDA0002373678050000061
wherein X is selected from
Figure BDA0002373678050000062
Figure BDA0002373678050000063
And substituted groups thereof;
wherein Q is an unsubstituted alkyl, substituted alkyl, unsubstituted alkenyl, substituted alkenyl, unsubstituted alkynyl, substituted alkynyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl group;
wherein R is10-R13Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, alkoxycarbonyl, ethyl, butyl, tert-butyl, -C- (CH)3)3、
Figure BDA0002373678050000064
(3, 5-di-tert-butyl) Ph, fluorine,
Figure BDA0002373678050000065
Wherein R isxAnd RyIndependently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, alkoxycarbonyl, ethyl, butyl, tert-butyl, -C- (CH)3)3(3, 5-di-tert-butyl) Ph, fluorine or
Figure BDA0002373678050000071
And
wherein R is10-R12Wherein each pair of adjacent R groups is independently one or two separate groups or atoms or fused to form a 5-6 membered ring, and
wherein R is10-R12Represents single, double, triple, quadruple or no substitution.
Additional advantages of the disclosed methods and compositions will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the disclosed methods and compositions. The advantages of the disclosed methods and compositions will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention as claimed.
Brief Description of Drawings
The present invention is illustrated in the figures of the accompanying drawings which are meant to be exemplary and not limiting, in which like references are intended to refer to the same or corresponding parts, and in which:
FIG. 1 graphically presents photoluminescence characteristics of emitters used in an exemplary color-stabilized OLED device according to one or more embodiments herein;
FIG. 2 presents in graphical form an OLED structure according to one or more embodiments herein;
FIG. 3 presents compounds for use as OLED emitters according to one or more embodiments herein;
FIG. 4 presents compounds for use as OLED emitters according to one or more embodiments herein;
FIG. 5A presents compounds for use as OLED emitters according to one or more embodiments herein;
FIG. 5B graphically represents an emission spectrum of an exemplary OLED device employing the compound of FIG. 5A implemented in accordance with one or more embodiments herein;
FIG. 6 presents compounds for use as OLED emitters according to one or more embodiments herein;
FIG. 7 presents compounds for use as OLED emitters according to one or more embodiments herein;
FIG. 8 graphically represents an emission spectrum of an exemplary color-stable OLED device;
FIG. 9 graphically represents the emission spectra of 6 exemplary OLED devices;
FIG. 10 graphically represents the emission spectrum and electroluminescent properties of another exemplary OLED device;
fig. 11 graphically presents the EQE%, power efficiency, and emission spectra of 6 additional exemplary OLED devices;
FIG. 12 graphically depicts emission spectra and electroluminescent properties of another exemplary OLED device;
FIG. 13 graphically depicts emission spectra and electroluminescent properties of another exemplary OLED device; and
fig. 14 presents the spectrum of the OLED device when the voltage is tuned and the efficiency of the OLED device as a function of brightness.
Detailed Description
The disclosed methods and compositions may be understood more readily by reference to the following detailed description of specific embodiments and the examples included therein and to the figures and their previous and following description.
I. Definition of
Throughout the specification, terms may have subtle meanings implied or implied by context beyond the meanings explicitly stated. Likewise, the phrase "in one embodiment" as used herein does not necessarily refer to the same embodiment, and the phrase "in another embodiment" as used herein does not necessarily refer to a different embodiment. Similarly, the phrase "one or more embodiments" as used herein does not necessarily refer to the same embodiment, and the phrase "at least one embodiment" as used herein does not necessarily refer to a different embodiment. It is intended, for example, that claimed subject matter, in whole or in part, include combinations of exemplary embodiments.
As used herein, the term "alkyl" is a branched or unbranched saturated hydrocarbon group having 1 to 24 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl and the like. "lower alkyl" groups are alkyl groups containing 1 to 6 carbon atoms. Likewise, "lower alkenyl" and "lower alkynyl" have similar chain lengths. The alkyl group may also contain one or more heteroatoms within the carbon skeleton. Examples include oxygen, nitrogen, sulfur, and combinations thereof. In some embodiments, the alkyl group contains 1-4 heteroatoms. The term "alkyl" includes both "unsubstituted alkyls" and "substituted alkyls," the latter of which refers to alkyl moieties having one or more substituents replacing a hydrogen on one or more carbon atoms of the hydrocarbon backbone. Such substituents include, but are not limited to, halogen, hydroxy, carbonyl (e.g., carboxy, alkoxycarbonyl, formyl, or acyl), thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, amido, amidine, imine, cyano, nitro, azido, mercapto, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamide, sulfonyl, heterocyclyl, aralkyl, or an aromatic or heteroaromatic moiety.
As used herein, the term "alkoxy" is an alkyl group bound through a single terminal ether linkage; that is, "alkoxy" may be defined as — OR, where R is alkyl as defined above. "lower alkoxy" is an alkoxy group containing 1 to 6 carbon atoms.
As used herein, the term "alkenyl" is a hydrocarbyl group having from 2 to 24 carbon atoms and a structural formula comprising at least one carbon-carbon double bond. Asymmetric structures such As (AB) C ═ C (cd) are intended to include both the E and Z isomers. The presence of E and Z isomers in the structural formulae herein in which asymmetric olefins are present is presumed or can be unambiguously represented by the bond symbol C. The term "alkenyl" includes both "unsubstituted alkenyls" and "substituted alkenyls," the latter of which refers to alkenyl moieties having one or more substituents replacing a hydrogen on one or more carbon atoms of the hydrocarbon backbone.
As used herein, the term "alkynyl" is a hydrocarbon group having from 2 to 24 carbon atoms and a structural formula comprising at least one carbon-carbon triple bond. The term "alkynyl" includes both "unsubstituted alkynyls" and "substituted alkynyls," the latter of which refers to alkynyl moieties having one or more substituents replacing a hydrogen on one or more carbon atoms of the hydrocarbon backbone.
As used herein, the term "aryl" is any carbon-based aromatic group including, but not limited to, benzene, naphthalene, and the like. The term "aromatic radical" also includes "heteroaryl," which is defined as an aromatic radical having at least one heteroatom incorporated into the ring of the aromatic radical. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. The aryl group may be substituted or unsubstituted. The aryl group may be substituted with one or more groups including, but not limited to, alkyl, alkynyl, alkenyl, aryl, halo, nitro, amino, ester, ketone, aldehyde, hydroxy, carboxylic acid, or alkoxy.
As used herein, the term "cycloalkyl" is a non-aromatic carbon-based ring consisting of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term "heterocycloalkyl" is a cycloalkyl group as defined above in which at least one of the ring carbon atoms is substituted with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.
As used herein, the term "aralkyl" is an aryl group having an alkyl, alkynyl or alkenyl group as defined above attached to an aromatic group. An example of an aralkyl group is benzyl.
As used herein, the term "hydroxyalkyl" refers to an alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, haloalkyl or heterocycloalkyl group as described above having at least one hydrogen atom substituted with a hydroxyl group.
The term "alkoxyalkyl" is defined as an alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, haloalkyl, or heterocycloalkyl group as described above with at least one hydrogen atom substituted with an alkoxy group as described above.
As used herein, the term "ester" is represented by the formula-c (o) OA, wherein a can be alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl as described above.
As used herein, the term "carbonate group" is represented by the formula-oc (o) OR, wherein R can be hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, haloalkyl, OR heterocycloalkyl as described above.
As used herein, the term "carboxylic acid" is represented by the formula-C (O) OH.
As used herein, the term "aldehyde" is represented by the formula-C (O) H.
As used herein, the term "keto" is represented by the formula-c (o) R, wherein R is alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, haloalkyl, or heterocycloalkyl as described above.
As used herein, the term "carbonyl" is represented by the formula-C ═ O.
As used herein, the term "ether" is defined by the formula AOA1Is represented by the formula, wherein A and A1May independently be an alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group as described above.
As used herein, the term "carbocycle" or "carbocyclyl" refers to a stable 3,4, 5, 6, or 7 membered monocyclic or bicyclic or 7, 8, 9, 10, 11, 12, or 13 membered bicyclic or tricyclic ring, any of which may be saturated, partially unsaturated, or aromatic. Illustrative but non-limiting carbocycles can include cyclopropyl, cyclobutyl, cyclobutenyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, adamantyl, cyclooctyl, cyclooctenyl, cyclooctadienyl, [3.3.0] bicyclooctane, [4.3.0] bicyclononane, [4.4.0] bicyclodecane, [2.2.2] bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, and anthracenyl.
Bridged rings occur when one or more carbon atoms connect two non-adjacent carbon atoms. Preferred bridges are one or two carbon atoms. Note that bridges always convert a single ring into a double ring. When a ring is bridged, the substituents set forth for that ring may also be present on the bridge. These terms are also intended to include "aryl".
The term "heterocycle" or "heterocyclyl" as used herein refers to a cyclic group attached via a ring carbon or nitrogen of a mono-or bicyclic ring comprising 3 to 10 ring atoms (preferably 5 to 6 ring atoms) and optionally comprising one or more double or triple bonds, and optionally substituted with one or more substituents, said ring atoms including carbon and 1 to 4 heteroatoms, each selected from oxygen, sulfur and n (Y) in a non-peroxide form, wherein Y is absent or is H, O, (C) Y1-4) Alkyl, phenyl or benzyl. The term "heterocycle" also encompasses substituted and unsubstituted heteroaryl rings. Examples of heterocycles include, but are not limited to, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzoxazolinyl, benzothiazolyl, benzotriazolyl, benzotetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl, carbazolyl, 4aH carbazolyl, carbolinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, 2H,6H-1,5, 2-dithiazinyl, dihydrofuro [2,3b ] and]furyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isatinoyl, isobenzofuryl, imidazolyl, indazolyl, indazolinyl, indolyl, indazolinyl, indolyl, etc,Isochroman group, isoindolyl group, isoindolinyl group, isoindolyl group, isoquinolyl group, isothiazolyl group, isoxazolyl group, methylenedioxyphenyl group, morpholinyl group, naphthyridinyl group, octahydroisoquinolyl group, oxadiazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,3, 4-oxadiazolyl group, oxazolidinyl group, oxazolyl group, oxindolyl group, pyrimidinyl group, phenanthridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxathiin group, phthalazinyl group, piperazinyl group, piperidinyl group, piperidonyl group, 4-piperidonyl group, piperonyl group, pteridinyl group, purinyl group, pyranyl group, pyrazinyl group, pyrazolidinyl group, pyrazolyl group, pyridazinyl group, pyridooxazole, pyridothiazole, pyridyl group, pyrimidinyl group, pyrrolidinyl group, pyridoxalyl group, pyridothiazole group, pyrido, Pyrrolinyl, 2H-pyrrolyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrazolyl, 6H-1,2, 5-thiadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thienyl, and xanthenyl.
The term "heteroaryl" as used herein refers to a monocyclic aromatic ring comprising 5 or 6 ring atoms, said ring atoms comprising carbon and 1,2,3 or 4 heteroatoms, each heteroatom being selected from the group consisting of oxygen in non-peroxide form, sulfur and n (Y), wherein Y is absent or is H, O, (C)1-C8) Alkyl, phenyl or benzyl. Non-limiting examples of heteroaryl groups include furyl, imidazolyl, triazolyl, triazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyrrolyl, pyrazinyl, tetrazolyl, pyridyl (or its N-oxide), thienyl, pyrimidinyl (or its N-oxide), indolyl, isoquinolyl (or its N-oxide), quinolyl (or its N-oxide), and the like. The term "heteroaryl" may include mono-fused (ortho-fused) bicyclic heterocyclic groups of about 8 to 10 ring atoms derived therefrom, particularly benzo derivatives or rings obtained by fusing them with propylene, trimethylene or tetramethylene diyl. Examples of heteroaryl groups include, but are not limited toFuryl, imidazolyl, triazolyl, triazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyrrolyl, pyrazinyl, tetrazolyl, pyridyl (or its N-oxide), thienyl, pyrimidinyl (or its N-oxide), indolyl, isoquinolyl (or its N-oxide), quinolyl (or its N-oxide), and the like.
As used herein, the term "halogen" refers to fluorine, chlorine, bromine or iodine.
As used herein, the term "substituted" refers to all permissible substituents of compounds described herein. In the broadest sense, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds. Exemplary substituents include, but are not limited to, halogen, hydroxyl, or any other organic group containing any number of carbon atoms, preferably 1 to 14 carbon atoms, and optionally containing one or more heteroatoms such as oxygen, sulfur, or nitrogen in a linear, branched, or cyclic configuration to form a group. Representative substituents include alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, phenyl, substituted phenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, hydroxy, alkoxy, substituted alkoxy, phenoxy, substituted phenoxy, aryloxy, substituted aryloxy, alkylthio, substituted alkylthio, phenylthio, substituted phenylthio, arylthio, substituted arylthio, cyano, isocyano, substituted isocyano, carbonyl, substituted carbonyl, carboxyl, substituted carboxyl, amino, substituted amino, amido, substituted amido, sulfonyl, substituted sulfonyl, sulfonic acid, phosphoryl, substituted phosphoryl, phosphonyl, substituted phosphonyl, polyaryl, substituted polyaryl, C3-C20Cyclic radical, substituted C3-C20Cyclyl, heterocyclyl, substituted heterocyclyl, amino acids, peptides and polypeptide groups.
A heteroatom such as nitrogen may have a hydrogen substituent and/or any permissible organic compound substituent described herein that satisfies the valence of the heteroatom. It is understood that "substitution" or "substituted" includes the implicit condition that such substitution is commensurate with the valency allowed for the atom and substituent being substituted, and that such substitution results in a stable compound, i.e., a compound that does not spontaneously undergo transformation, e.g., by rearrangement, cyclization, elimination, and the like.
The numerical ranges disclosed herein disclose each and every possible number within the range and any subranges and combinations of subranges subsumed therein, respectively. For example, the carbon range (i.e., C)1-C10) It is intended that each possible carbon value and/or subrange contained therein be individually disclosed. E.g. C1-C10Carbon Length range of C1、C2、C3、C4、C5、C6、C7、C8、C9And C10And discloses sub-ranges contained therein, e.g. C2-C9、C3-C8、C1-C5And the like. Similarly, a range of integer values from 1-10 discloses individual values 1,2,3, 4, 5, 6, 7, 8, and 10 and subranges encompassed therein. Further, ranges such as external quantum efficiency, Color Rendering Index (CRI), and power efficiency, etc., disclose the individual values and fractions thereof (e.g., 1%, 1.1%, 1.2%, 1.32%, 1.48%, etc.) and subranges encompassed therein.
Organic Light Emitting Diodes (OLED)
The present disclosure describes platinum emitter (pt (ii) compounds) for use in voltage-driven, color-tunable OLEDs, the OLED devices themselves, and methods of making and using such pt (ii) emitter OLED devices. In one aspect, an OLED device employs a single emitter as described herein to generate light. Single emitter OLEDs simplify device structures and reduce manufacturing costs compared to multi-emitter OLEDs or more complex OLEDs, such as those incorporating two or more sub-OLEDs. In one or more embodiments described herein, emitters are provided whose emission wavelength is varied in response to tuning a drive voltage or current to achieve a desired color or color temperature. When a voltage is applied, the OLED produces varying monomer emission (e.g., 480-530nm) and excimer emission (e.g., 600-650nm) to produce light having wavelengths along the visible spectrum (e.g., about 480-800 nm). By varying the drive voltage or current, the ratio of emitter monomer emission to excimer emission can be varied to produce different colors. Fig. 1 shows the photoluminescence characteristics of an exemplary OLED device, and in particular, it shows monomeric and excimer ("aggregate state emission") emission peaks across the visible spectrum. Here, the monomer emission peak is at about 510nm, while the excimer emission peak is at about 625 nm.
The emitter and OLED devices described herein advantageously provide light emission characteristics suitable for use in typical OLED device applications. The OLED device as described herein includes a response rate between 1 μ s and 1ms, and can function at voltages as low as 2.4V. In one or more embodiments, the OLED device produces 5000cd/m at voltages as low as 5V2Or higher brightness. In one or more embodiments, the OLED device achieves an EQE greater than 10%, 15%, 20%, or more. Further, the OLED devices described herein can produce Color Rendering Index (CRI) values of 70, 75, 80, 85, 90, 95 or higher using the single platinum emitters described herein.
These characteristics are improved compared to conventional multi-emitter or non-voltage tunable OLED devices. For example, the conventional method is at 1000cd/m2-5000cd/m2With a strong efficiency roll-off and a low EQE at luminance values in between, which is a common luminance value in the art. Furthermore, existing single emitter OLED devices cannot achieve CRI values above 80 without relying on multiple emitters.
It is important to note that the platinum emitters described herein do not employ various conventional color tuning strategies. For example, the emitter does not tune color according to doping concentration (i.e., change the concentration of polar dopant molecules in the emissive layer or host material). The OLED devices described herein do not employ P-I-N doped layers as known in the art. The hole transport layer is not p-doped and the electron transport layer is not n-doped.
Furthermore, to produce a certain color, the OLEDs described herein do not use a multiple OLED arrangement of the following array: each OLED in the array is specifically tuned such that the average of the colors produces the desired color. In addition, the OLEDs herein do not rely on fluorescent molecules inserted into phosphorescent complexes, some ligands that fine tune the emission color, or ligands that capture carriers (carriers). In contrast, the voltage dependent color tunable nature of OLEDs avoids the use of these approaches.
Notably, the OLED devices described herein also do not include a carrier blocking layer or a hole blocking layer disposed between adjacent emissive layers to provide color tunable functionality. In one or more embodiments, the OLED devices described herein include a single emissive layer and a co-host (co-host) mixture is utilized in the emissive layer. In one or more embodiments, the OLED devices described herein include an emissive layer that can be divided into two sub-emissive layers. In the first sub-emissive layer, the emitter and host mixture is selected to produce a monomer emission as the primary emission. In the second sub-emissive layer, the emitter and host mixture is selected to produce excimer or aggregate state emission as the dominant emission.
Referring now to FIG. 2, as a non-limiting example, a color tunable OLED structure 100 with a single emitter as in one or more embodiments described herein is shown. Methods of manufacturing OLEDs are known. The OLED 100 includes a pair of electrodes corresponding to an anode 105 and a cathode 110, which sandwich a plurality of semiconductor layers between the two electrodes, which cause electroluminescence when a voltage is applied to the OLED. The anode 105 and cathode 110 include metallic materials for electrical conduction, such as the following non-limiting examples: aluminum, gold, magnesium or barium for the cathode, and indium tin oxide ("ITO") for the anode. The anode 105 and cathode 110 may have a thickness between 100-200 nm. In one or more embodiments, the anode 105 is further placed on top of a suitable substrate 112. The substrate 112 emits light generated by the OLED 100 and is generally made of a transparent material. For example, the substrate 112 may be made of glass or a transparent polymer.
A hole injection layer ("HIL") 115 and a hole transport layer ("HTL") 120 are stacked on top of the anode 105. These layers play a role in adjusting electron/hole injection to achieve transport balance of charge carriers in the emissive layer 125 of the OLED 100. In one or more embodiments, HIL115 has a thickness between 1-10nmAnd (4) degree. In one or more embodiments, the HTL 115 has a thickness between 30-80 nm. The materials of the HIL115 and HTL 120 are selected to maximize OLED efficiency. As some non-limiting examples, the HIL115 may comprise molybdenum trioxide ("MoO3") or hexaazatriphenylenehexacyano (" HAT-CN "), and the HTL 120 may comprise tris (4-carbazol-9-ylphenyl) amine (" TcTa "), N '-bis (1-naphthyl) -N, N' -diphenyl- (1,1 '-biphenyl) -4, 4' -diamine (" NPB "), or bis-4-tolylaminophenylcyclohexane (" TAPC "). In one or more embodiments, the HTL 120 includes two complementary sublayers. For example, a first sub-layer of the HTL 120 may include deposited TAPC or NPD, while a second sub-layer may include deposited TcTa. Exemplary compound structures deposited in the HIL115 and HTL 120 are shown below.
Figure BDA0002373678050000151
Other suitable HIL and/or HTL materials may be used, as known in the art.
An emissive layer 125 is disposed on top of the HTL 120. In one or more embodiments, the emissive layer 125 is between 10-30nm thick. In one or more embodiments, emissive layer 125 comprises one or more host materials mixed with an emitter formed from a compound described herein, examples of which are:
Figure BDA0002373678050000152
Figure BDA0002373678050000161
the host material may be formed from a single host (i.e., one host mixed with the emitter) or may be formed as a joint host mixture (i.e., two hosts mixed with the emitter). The emitters are added to the host material in a percentage of the total weight. When a voltage is applied to the emission layer 125, the single emitter emits light.
In one or more embodiments, the emissive layer 125 employs a single layer structure that combines host mixtures (e.g., two host materials and an emitter). In other embodiments, emissive layer 125 is two separate sub-emissive layers, where the emitters are mixed with one or more hosts in each sub-layer ("dual EML"). For example, the emissive layer 125 may be a single-host dual EML, where a first host is mixed with the emitter in a first sub-emissive layer and a second host is mixed with the emitter in a second sub-emissive layer. The first body may be the same or different from the second body. In other embodiments, the emissive layer 125 is a joint host dual EML structure, where a first sub-layer includes two host materials mixed with the emitter and a second sub-layer includes two host materials also mixed with the emitter. The joint host material in the first and second sub-layers may be the same or different. In still other embodiments, emissive layer 125 is arranged as a hybrid single/combined host dual EML. For example, the first sublayer may include a first host mixed with the emitter, and the second sublayer may include a second host and a third host mixed with the emitter as a joint host. The first, second and third bodies may be made of the same or different materials. As for the emission layer 125, more than one emitter may be used as needed, regardless of whether the emission layer is formed of a single layer or separate sub-emission layers.
As some non-limiting examples, the host material may be TcTa, 1, 3-bis (N-carbazolyl) benzene ("MCP"), 4, 6-bis (3, 5-di-3-pyridylphenyl) -2-methylpyrimidine ("B3 PymPm"), or 2, 6-bis (3- (9H-carbazol-9-yl) phenyl) pyridine ("26 Dczppy"). Other suitable host materials may be used, as known in the art. In some embodiments, emissive layer 125 is a single layer structure comprising one or more hosts (as described above) and X% of one or more composite emitters (e.g., Pt-X-1 to Pt-X-6) by weight of the hosts contained therein, where X is between 2% and 30%, 2% and 25%, 2% and 20%, or 2% and 15%. In some other embodiments, emissive layer 125 is formed from individual sub-emissive layers, each of which independently comprises one or more hosts as described above and one or more composite emitters (e.g., Pt-X-1 to Pt-X-6) in an amount of X% by weight of the hosts contained therein, wherein X is between 2% and 30%, 2% and 25%, 2% and 20%, or 2% and 15%. In particular embodiments, emissive layer 125 is a combined host monolayer structure comprising TcTa and B3 PymPxm as a combined host and X% of a composite emitter (e.g., Pt-X-3 or Pt-X-5) by weight of the host, where X is between 2% to 30%, 2% to 25%, 2% to 20%, or 2% to 15%.
Figure BDA0002373678050000171
An electron transport layer ("ETL") 130 and an electron injection layer ("EIL") 135 are disposed on top of the emission layer 125 and below the cathode 110. These layers provide high electron affinity and high electron mobility to the OLED 100 to allow electrons to flow through the various OLED layers. In one or more embodiments, the ETL 130 has a thickness of 30-80 nm. In one or more embodiments, the EIL 135 has a thickness of 1-5 nm. In one or more embodiments, additional electron transport materials are added to the ETL 130 and ETL 135 to facilitate electron emission. The materials used for the ETL 130 and the EIL 135 are selected to maximize OLED efficiency. As some non-limiting examples, the ETL 130 may comprise B3PymPm, 1,3, 5-tris (m-pyridin-3-ylphenyl) benzene ("tmpyppb"), 2,4, 6-tris [3'- (pyridin-3-yl) biphenyl-3-yl ] -1,3, 5-triazine ("tmppppytz"), or 2, 2', 2 "- (1,3, 5-benzenetriyl) -tris (1-phenyl-1-H-benzimidazole) (" TPBi "). As some non-limiting examples, EIL 135 may comprise LiF, lithium 8-hydroxy-quinoline ("Liq"), Cs, or CsF.
Figure BDA0002373678050000181
Other suitable EIL and/or ETL materials may be used, as known in the art.
Metal complex emitters
In one or more embodiments, the emitters used as dopants in the emissive layer 125 described above are metal composites having a square planar chemistry. For example, the metal complex is a platinum (II) complex. Platinum complexes are preferred because they have a rigid ligand backbone with multidentate chelates to minimize structural distortion upon excitation, have extended ligand pi-conjugation, have strong delta-donation (e.g., O-N ^ C ^ N with deprotonated C donors) to ensure strong metal-ligand interactions, and have high metal characteristics or charge transfer participation in the emission state (i.e., short emission lifetime of the emitter). In one or more embodiments, the emitter is a compound having the structure form of Pt (O ^ N ^ C ^ N).
As indicated above, specific embodiments of platinum emitters suitable for use as single emitters in OLED devices as described herein are shown. Pt-X-1, Pt-X-2, Pt-X-3, Pt-X-4, Pt-X-5, and Pt-X-6 may each be mixed with one or more host materials in an emissive layer (e.g., emissive layer 125). In each emitter Pt-X-1, Pt-X-2, Pt-X-3, Pt-X-4, Pt-X-5, and Pt-X-6, the emitter includes an N ^ C ^ N ligand and incorporates an additional phenol/indenyl moiety into an N ^ C ^ N main frame (mainframe). The strong ligand field presence is generated by two strong sigma donations (O-donor and C-donor). This results in strong metal-ligand interactions and provides strong emission characteristics. Minor structural deformation is also desirable, which is a rigid structure imposed by the fused 6-5-membered metallocycle compound.
The Pt-X-1, Pt-X-2, Pt-X-3, Pt-X-4, Pt-X-5, and Pt-X-6 emitters are all platinum complexes (Pt (II)).
In one or more embodiments, the emitter is a platinum (II) complex having the following basic structure:
Figure BDA0002373678050000191
in one or more embodiments, X is independently a 5 or 6 membered carbocyclic or heterocyclic ring. In one or more embodiments, R1-R3Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, unsubstituted alkenyl, substituted alkenyl, unsubstituted alkynyl, substituted alkynyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, hydroxyl, carboxyl, alkoxy, amino, nitro, amido, aryl, alkoxy, amino, nitro, amido, aralkyl, cyano, carboxyl, mercapto, cyano, carboxyl, alkoxy, mercapto, carboxyl, alkoxy, amino,A styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl group. In one or more embodiments, R4Independently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, sulfonyl, phosphino, and combinations thereof. In one or more embodiments, R1-R4Independently selected from the group consisting of: hydrogen, halogen, alkyl, ethyl, butyl, tert-butyl, -C- (CH)3)3、
Figure BDA0002373678050000192
(3, 5-di-tert-butyl) Ph, fluorine,
Figure BDA0002373678050000193
Or
Figure BDA0002373678050000194
In one or more embodiments, RxAnd RyIndependently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, phosphino, and combinations thereof. In one or more embodiments of the above infrastructure, two or more adjacent R' s1、R2、R3、R4Optionally joined to form fused rings. For example, R1And R2Fused rings may be formed, such as in Pt-X-1 and Pt-X-2. In one or more embodiments, R1-R4Each pair of adjacent R groups in (a) is independently two separate groups (or atoms) or one group (or atom) and forms a 5-6 membered ring. In one or more embodiments, R1-R4Represents one or more substitutions such as mono-, di-, tri-, tetra-or unsubstituted.
In one or more embodiments, the emitter is a platinum (II) complex having the following basic structure:
Figure BDA0002373678050000201
in one or more embodiments, R6-R8Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, unsubstituted alkenyl, substituted alkenyl, unsubstituted alkynyl, substituted alkynyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl groups. In one or more embodiments, R4Independently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, sulfonyl, phosphino, and combinations thereof. In one or more embodiments, X is independently a 5 or 6 membered carbocyclic or heterocyclic ring. In some embodiments, X may be selected from:
Figure BDA0002373678050000202
and substituted groups thereof. In one or more embodiments, R5-R9Independently selected from the group consisting of: hydrogen, halogen, alkyl, ethyl, butyl, tert-butyl, -C- (CH)3)3、
Figure BDA0002373678050000211
(3, 5-di-tert-butyl) Ph, fluorine,
Figure BDA0002373678050000212
Or
Figure BDA0002373678050000213
In one or more embodiments, RxAnd RyIndependently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, phosphino, and combinations thereof. In one or more embodiments of the above infrastructure, two or more adjacent R' s5、R6、R7、R8、R9Optionally joined to form fused rings. In one or more embodiments, R5-R9Each pair of adjacent R groups in (a) is independently two separate groups (or atoms) or one group (or atom) and forms a 5-6 membered ring. In one or more embodiments, R5-R9Represents one or more substitutions such as mono-, di-, tri-, tetra-or unsubstituted.
In one or more embodiments, the emitter is a platinum (II) complex having the following basic structure:
Figure BDA0002373678050000214
in one or more embodiments, R10-R13Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, unsubstituted alkenyl, substituted alkenyl, unsubstituted alkynyl, substituted alkynyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, thio, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl groups. In one or more embodiments, each Y group is independently a 5 or 6 membered carbocyclic or heterocyclic ring. In some cases, Q is unsubstituted alkyl, substituted alkyl, unsubstituted alkenyl, substituted alkenyl, unsubstituted alkynyl, substituted alkynyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxyl, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonylA carbonyl group. In some cases, Q is alkynyl, such as cyano. In some embodiments, X may be selected from:
Figure BDA0002373678050000221
Figure BDA0002373678050000222
or
Figure BDA0002373678050000223
And substituted groups thereof. In one or more embodiments, R10-R13Independently selected from the group consisting of: hydrogen, halogen, alkyl, ethyl, butyl, tert-butyl, -C- (CH)3)3、
Figure BDA0002373678050000224
(3, 5-di-tert-butyl) Ph, fluorine,
Figure BDA0002373678050000225
Or
Figure BDA0002373678050000226
In one or more embodiments, RxAnd RyIndependently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylate, nitrile, isonitrile, sulfanyl, sulfinyl, phosphino, and combinations thereof. In one or more embodiments of the above infrastructure, two or more adjacent R' s10、R11、R12、R13Optionally joined to form fused rings. In one or more embodiments, R5-R9Each pair of adjacent R groups in (a) is independently two separate groups (or atoms) or one group (or atom) and forms a 5-6 membered ring. In one or more embodiments, R5-R9Represents one or more substitutions such as mono-, di-, tri-, tetra-or unsubstituted.
Voltage-dependent color tunability of OLEDs
In one aspect, the emitters described herein are voltage-dependent tunable emitters, and utilize different states of a single emitter to produce different colors of light across the visible spectrum. The compounds herein produce white light by applying a voltage to produce complementary monomer and aggregate (e.g., excimer) emissions upon excitation. This balance results in high photoluminescence quantum yield and shorter emission lifetimes (approximately 100ns to 10 μ s), leading to high CRI and yielding efficient OLED illumination. In one or more embodiments, the devices described herein may additionally utilize dual host doping or dual emissive layers to greatly increase the color tuning range, increase brightness: (brightness)>80,000cd/m2) And suppress the efficiency roll-off at high luminance (from 1000 cd/m)2To 5000cd/m2)). Dual-host doping (or joint host doping) refers to the addition of a complex dopant to a dual-host mixture in a single emissive layer.
Monomer emission and excimer emission can be amplified or suppressed by constructing the emission layers with different emitter doping concentrations. For example, at low doping concentrations (e.g., 2-6% by weight of the emissive layer), the monomer emission dominates and results in an OLED device that is more color stable at 480-530nm wavelength when it is voltage tuned. At higher doping concentrations (e.g., 15 to 30 wt% of the emissive layer, and more particularly, between 20 to 25 wt%), excimer emission dominates and the OLED device is more color stable at 600-700 nm. By employing dual EMLs, the OLED device can be extended to the entire visible spectral range.
In one aspect, a method is provided for fabricating a voltage-dependent color tunable OLED device having a single emitter to produce white light. To form white light, OLED devices combine the emissions from two sources in a single emitter. In some embodiments, a single emitter produces emission from both a monomeric state and an excimer state. In other embodiments, the single emitter includes additional host materials to facilitate emission from the monomer state and the excited complex state. In other embodiments, a single emitter produces both high-energy fluorescence at 450nm to 550nm and low-energy phosphorescence at 560nm to 700nm at different drive voltages or currents.
Next, the method applies a low voltage of 2.4V to 6V to the emitter to generate emission from one of the two emission sources. For example, at low voltages, the emission is dominated by low energy excimer emission, excited complex emission, or phosphorescent emission, depending on the implementation. At low voltages, OLED devices emit predominantly light of longer wavelengths in the visible spectrum, such as red or orange light. However, as the driving voltage is increased from 6V to 12V, the emission (emissions) emits a large amount of light and/or fluorescence in a high-energy monomer state. The more the voltage is increased, the more dominant the high-energy emission is with respect to the low-energy emission, and as a result the shorter the wavelength of the emitted light. For example, at a voltage of 3V, the OLED device produces a wavelength of 650nm, and at a voltage of 8V, the OLED device produces a wavelength of 515 nm. In this way, the emission state of a single emitter can be changed by changing the level of the driving voltage, thereby tuning the OLED to a different color.
In one or more embodiments, the EQE ranges between 15-20% or 20-25%. This is advantageous because the EQE of conventional color tunable OLED emitters is typically less than 15%. In one or more embodiments, the low efficiency roll-off is at 1000-2Within the range of (1).
Examples
The following are examples illustrating embodiments for practicing the disclosure described herein. These examples should not be construed as limiting. These embodiments are performed using an OLED device having multiple layers, compositions, and materials as in OLED 100, where the platinum composite used as the emitter is 2% to 30% by weight of the emissive layer. Each OLED includes an anode 105, a cathode 110, a HIL115, a HTL 120, an ETL 130, and an EIL 135 as described herein. The emissive layer of each device varies from emitter to emitter and host material to produce different voltage-dependent color tunable OLED devices.
For devices with low emitter concentrations (4 wt%), only monomer emission occurs, and therefore the emitter color stabilizes as the voltage increases. FIG. 4 shows an exemplary color-stable emission spectrum of a Pt-X-2 emitter doped with a 4 wt% OLED when the voltage is increased from 3V to 14V in 1V increments. It can be seen that the intensity peaks around 520nm regardless of the voltage and then drops. This clear peak is generated because each pt (ii) molecule is separated by the host by using a low emitter doping concentration of 4 wt%. Then, the interaction between Pt (ii) molecules is weak, and the Pt emitter generates only monomer in the emission layer, so that only monomer emission can be observed over the entire driving voltage range (e.g., 3V to 10V). Thus, the OLED device can be said to be color stable. The experiments described are consistent with this color stability performance.
Pt-X-5 based OLEDs
a. Experiment 1
In a first example, the compound Pt-X-5 was prepared as an emitter in 6 OLED devices as described herein, each device having a different emissive layer. The OLED device was constructed according to the following structure: ITO anode, 100nm aluminum cathode, 2nmMoO3A HIL layer, a 50nm TAPCHTL layer, an additional 10nm TcTa HTL layer, a 50nm B3 PymPmETL layer, and a 1.2nm LiF EIL layer. The emissive layer of each of the 6 devices was then prepared using TcTa and B3PymPm as host materials. 5 of the OLED devices were fabricated as dual EMLs, and one was fabricated with a single emissive layer. Table 1 below shows the different amounts of emitter by weight. For example, device 1 has 4% Pt-X-5 compared to TcTa and 18% Pt-X-5 compared to B3 PymPmm.
Figure BDA0002373678050000251
TABLE 1
A voltage was then applied to each device and the emission intensity and wavelength were observed as the voltage was varied between 3V and 8V in 0.5V increments. The variation of the emission spectra of each of the 6 devices is shown in fig. 5 and shows how the intensity as a function of wavelength varies with voltage. For example, at low voltages (e.g., 2.5V-4V), the intensity peak is approximately 640nm-700nm, which corresponds to red light. However, at high voltages (e.g., 6V-8V), the intensity peaks at about 500-550nm, which corresponds to blue, green, and yellow light, respectively. Thus, the OLED device produces different colors with voltage.
Table 1 also illustrates information about: emission layer composition, EQE%, maximum power efficiency, maximum luminance, minimum voltage to start OLED emission (yield 1 cd/m)2"turn-on voltage"), and colors according to the x, y coordinate system of the International Commission Illumination (CIE). It can be seen that each of the 6 devices is for over 1000cd/m2Maintains an EQE% greater than 15% and includes a CRI in excess of 90. This is in contrast to conventional color tunable OLED devices, which are more than 1000cd/m2It is impossible to maintain an EQE of more than 15% and the CRI of its best device is no greater than 70, typically in the range of 40-70.
b. Experiment 2
In a second example, Pt-X-5 emitters were used to make a dual EML OLED device. The OLED device was constructed according to the following structure: ITO anode, 100nm aluminum cathode, 2nm MoO3A HIL layer, a 50nm TAPC HTL layer, an additional 10nm TcTaHTL layer, a 50nm TmPyPB ETL layer, and a 1.2nm LiF EIL layer. The dual EML consists of a 10nm first sublayer of TcTa mixed with 4 wt% Pt-X-5 and a 10nm second sublayer of 26Dczppy mixed with 20 wt% Pt-X-5. The voltage was then raised from 5V to 17V in 2V increments. The spectrum of the OLED device and the OLED device efficiency versus brightness when the voltage is tuned are shown in fig. 6. The performance of the OLED device during this experiment is shown in table 2 below.
Figure BDA0002373678050000261
TABLE 2
Pt-X-3 based OLEDs
c. Experiment 3
A third experiment was performed in which 6 additional OLED devices were constructed using a single emitter in the form of the compound Pt-X-3. The OLED device in this example was constructed in the following structure: ITO anode, 100nm aluminum cathode, 2nm MoO3A HIL layer, a 50nm TAPC HTL layer, an additional 10nm TcTa HTL layer, a 50nm B3 PymPmETL layer, and a 1.2nm LiFeIL layer. These 6 OLED devices were fabricated using Pt-X-3 as the single emitter, which Pt-X-3 was mixed with TcTa and B3 PymPmm as the combined host materials. In this experiment, each of the 6 units contained Pt-X-3 of different weight composition, as shown in Table 3 below. Device 1 is a color-stable OLED device (as shown in fig. 4) used as a reference; however, each of the remaining devices is voltage-dependent color tunable. Each of the 6 devices contains a single emissive layer, which is a dual EML, differing only by device 4. In the first sub-emissive layer of device 4, the Pt-X-3 emitter is 4 wt% compared to TcTa. In the second sub-emitter layer, the Pt-X-3 emitter was 18 wt% compared to the B3 PymPym. Then, the voltage was varied between 3V and 10V in 1V increments, and the intensity was observed. A plot of EQE%, power efficiency and emission spectra for different devices is shown in fig. 7.
Figure BDA0002373678050000262
Figure BDA0002373678050000271
TABLE 3
Pt-X-2 based OLEDs
d. Experiment 4
In a fourth embodiment, Pt-X-2 emitters are used in a dual EML OLED device with a CRI between 75-85. The OLED device was constructed according to the following structure: ITO anode, 100nm aluminum cathode, 2nm MoO3A HIL layer, a 50nm TAPC HTL layer, an additional 10nm TcTa HTL layer, a 50nm TmPyPB ETL layer, and a 1.2nm LiF EIL layer. The dual EML consists of a 10nm first sublayer mixed with 4 wt% of the combined body TcTa and B3 PymPxm of Pt-X-2 and a 10nm second sublayer mixed with 25 wt% of the combined body TcTa and B3 PymPxm of Pt-X-2. The voltage was then changed from 3V to 10V in 1V increments. The spectrum of the OLED device and the OLED device efficiency versus brightness when the voltage is tuned are shown in fig. 9. The monomer peak can be seen at about 480nm and the excimer peak can be seen at about 640 nm. The O isThe properties of the LED device during this experiment are shown in table 4 below.
Figure BDA0002373678050000272
TABLE 4
e. Experiment 5
In a fifth example, Pt-X-2 emitters were used to prepare dual EML OLED devices with CRI between 75-87. The OLED device was constructed according to the following structure: ITO anode, 100nm aluminum cathode, 2nm MoO3A HIL layer, a 50nm TAPCHTL layer, an additional 10nm TcTa HTL layer, a 50nm TmPyPB ETL layer, and a 1.2nm LiF EIL layer. The dual EML consisted of a 10nm first sublayer of host TcTa mixed with 4 wt% Pt-X-2 and a 10nm second sublayer of host 26Dczppy mixed with 20 wt% Pt-X-2. The voltage then changes from 5V to 15V in 2V increments. The spectrum of the OLED device and the efficiency versus brightness of the OLED device when the voltage is tuned are shown in fig. 10. The monomer peak can be seen at about 480nm and the excimer peak can be seen at about 640 nm. The properties of the OLED device during this experiment are shown in table 5 below.
Figure BDA0002373678050000281
TABLE 5
Pt-X-6 based OLEDs
d. Experiment 6
In a sixth embodiment, Pt-X-6 emitters were used to prepare dual EMLOLED devices with CRI between 72-78. The OLED device was constructed according to the following structure: ITO anode, 100nm aluminum cathode, 2nm MoO3A HIL layer, a 50 nmtpac HTL layer, an additional 10nm TcTa HTL layer, a 50nm TmPyPB ETL layer, and a 1.2nm LiF EIL layer. The dual EML comprises a 5-15nm first sub-layer of the host TcTa or CzSi mixed with 4 wt% Pt-X-2 and a 5-15nm second sub-layer of the host 26Dczppy mixed with 15-30 wt% Pt-X-6. The voltage was then varied from 5V to 15V in 1V increments. The spectrum of the OLED device and the OLED device efficiency versus brightness when the voltage is tuned are shown in fig. 14. A monomer peak can be seen at about 440nm,and an excimer peak can be seen at about 580 nm. The properties of the OLED device during this experiment are shown in table 6 below.
Figure BDA0002373678050000282
TABLE 6
The foregoing description of the specific embodiments will so fully reveal the general nature of the disclosure that others can, by applying knowledge within the skill of the relevant art (including the contents of the documents cited and incorporated herein), readily modify and/or adapt for various applications such specific embodiments, without undue experimentation, without departing from the general concept of the present disclosure. Therefore, such adaptations and modifications are intended to be within the meaning and range of equivalents of the disclosed embodiments, based on the teaching and guidance presented herein. It is to be understood that the phraseology or terminology herein is for the purpose of description and not of limitation, such that the terminology or phraseology of the present specification is to be interpreted by the skilled artisan in light of the teachings and guidance presented herein, in combination with the knowledge of one of ordinary skill in the relevant art.
While various embodiments of the present disclosure have been described above, it should be understood that they have been presented by way of example only, and not limitation. It will be apparent to persons skilled in the relevant art that various changes in form and detail can be made therein without departing from the spirit and scope of the disclosure. Thus, the present disclosure should not be limited by any of the above-described exemplary embodiments, but should be defined only in accordance with the following claims and their equivalents.

Claims (18)

1. A method of voltage tuning an OLED device having a pair of electrodes having opposite polarities, a plurality of organic layers disposed between the pair of electrodes, wherein at least one of the plurality of organic layers is an emissive layer, and wherein the emissive layer comprises a single emitter mixed with one or more host materials, wherein the emitter is an organic light emitting material or metal composite that is fluorescent or phosphorescent, and the emitter has both a singlet emission and an aggregate emission, the method comprising:
(a) providing a first voltage to the OLED device to cause the OLED device to emit a first color having a first wavelength; and
(b) adjusting the first voltage applied to the device to a second voltage to cause the OLED device to emit a second color having a second wavelength.
2. The method of claim 1, wherein the difference between the first voltage and the second voltage is 1V.
3. The method of claim 1, wherein the first voltage is 2.4V or higher.
4. A method of manufacturing a voltage tunable OLED device having a pair of electrodes having opposite polarities, a plurality of organic layers disposed between the pair of electrodes, wherein at least one of the plurality of organic layers is an emissive layer, the method comprising:
obtaining an emitter, wherein the emitter is a fluorescent or phosphorescent organic light emitting material or metal complex, and the emitter has both a monomer state emission and an aggregate state emission;
mixing the emitter with one or more host materials to build up an emissive layer,
wherein the weight percentage of the emitters of the emission layer is 2-30%.
5. The method of claim 4, wherein the emitter has the chemical structure: Pt-X-1, Pt-X-2, Pt-X-3, Pt-X-4, Pt-X-5, or Pt-X-6.
6. The method of claim 4, wherein the weight percentage of the emitters of the emissive layer is 2-6%.
7. The method of claim 4, wherein the weight percentage of the emitters of the emissive layer is 16-30%.
8. The method of claim 4, further comprising mixing the emitter with one or more host materials such that the emissive layer comprises a first sub-layer and a second sub-layer.
9. The method of claim 8, wherein the weight percentage of emitters of the first sublayer is 2-6%.
10. The method of claim 8, wherein the weight percentage of emitters of the second sublayer is 16-30%.
11. The method of claim 8, wherein the first sub-layer comprises one host material and the second sub-layer comprises two host materials.
12. The method of claim 8, wherein the first sublayer comprises two host materials and the second sublayer comprises two host materials.
13. The method of claim 8, wherein the first sub-layer emits singlet emission and the second sub-layer emits aggregate emission.
14. The method of claim 4, wherein the one or more host materials are selected from the group consisting of: TcTa, MCP, B3 PymPmm and 26 Dczppy.
15. The method of claim 4, wherein the OLED device is voltage-driven color tunable between 2.4V to 14V.
16. The method of claim 4, further comprising constructing the plurality of organic layers to include a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
17. The method of claim 4, wherein the emitter has a chemical structure according to:
Figure FDA0002373678040000021
wherein X is independently a 5 or 6 membered heterocyclic ring,
wherein R is1-R3Independently selected from the group consisting of: hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or alkoxycarbonyl groups,
wherein R is4Independently selected from the group consisting of: hydrogen, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, sulfonyl, phosphino, and combinations thereof,
wherein R is1-R3Each pair of adjacent R groups in (a) is independently one or two independent groups or atoms or is selected to form a 5-6 membered ring, and
wherein R is1-R3Represents single, double, triple, quadruple or no substitution.
18. The method of claim 4, wherein the emitter has a chemical structure according to:
Figure FDA0002373678040000031
wherein X is selected from:
Figure FDA0002373678040000032
wherein R is1-R4Independently selected from the group consisting of: hydrogen, halogen,Hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, alkoxycarbonyl, ethyl, butyl, tert-butyl, -C- (CH)3)3、
Figure FDA0002373678040000033
(3, 5-di-tert-butyl) Ph, fluorine or
Figure FDA0002373678040000034
Wherein R is5Independently selected from the group consisting of hydrogen, halogen, hydroxy, unsubstituted alkyl, substituted alkyl, cycloalkyl, unsubstituted aryl, substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, amido, aralkyl, cyano, carboxy, mercapto, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, alkoxycarbonyl, ethyl, butyl, tert-butyl, -C- (CH)3)3(3, 5-di-tert-butyl) Ph, fluorine or
Figure FDA0002373678040000035
And
R1–R4each pair of adjacent R groups in (a) together with other carbon or nitrogen atoms form a 5-8 membered ring.
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